19

Summerland Key, FL Homes for Sale under $500,000

Section Image Section Image
  • 22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    /6

    $499,000

    • Land

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042

    7049 sf Oceanfront Lot with beautiful views of Cudjoe Bay ! Build your dream home in Cudjoe Key ! Don't miss out on this great opportunity to build and live in one of the most desirable neighborhoods in the Keys !

    Agent Photo

    Emily Lombard

    Ocean Sotheby's International Realty

    (786) 659-1030

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    /39

    $495,000

    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 551-4336

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • 21865 Spain Blvd, Summerland Key, FL 33042
    21865 Spain Blvd, Summerland Key, FL 33042
    21865 Spain Blvd, Summerland Key, FL 33042
    /6

    $400,000

    • Land

    21865 Spain Blvd, Summerland Key, FL 33042

    Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (305) 614-8634

    21865 Spain Blvd, Summerland Key, FL 33042
  • 31052 Avenue H, Big Pine Key, FL 33043
    31052 Avenue H, Big Pine Key, FL 33043
    31052 Avenue H, Big Pine Key, FL 33043
    /13

    $475,000

    • 4 Beds
    • 3 Baths
    • 1,620 Sq Ft

    31052 Avenue H, Big Pine Key, FL 33043

    Investment opportunity on 10,000 sq. ft. double lot near the Big Pine Community Park; the location offers easy access to US1, local shopping and more; Marathon and Key West are within easy reach. **DO NOT WALK THE PROPERTY WITHOUT APPOINTMENT** 2 units, 2 tenants; pets on premises. 1,060 sq. ft. mobile home has 3BD/2BA, exterior wood siding; interior has been updated. CBS garage has 560 sq. ft.

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 646-1138

    31052 Avenue H, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    /19

    $465,000

    • Land

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

    Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    /30

    $485,000

    • 2 Beds
    • 1.5 Baths
    • 604 Sq Ft

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

    Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
  • 3 W Cook, Cook Island Key, FL 33043
    3 W Cook, Cook Island Key, FL 33043
    3 W Cook, Cook Island Key, FL 33043
    /8

    $489,500

    • 3 Beds
    • 2 Baths
    • 704 Sq Ft

    3 W Cook, Cook Island Key, FL 33043

    Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfront bungalow has two bedrooms, two baths, and an additional upstairs loft with panoramic views of Cook Island, Atlantic and Coupon Bight. The house amenities include solar power, generator hookup, hot and cold water from rain collecting cistern, inverter a/c units, permitted septic system. Repairable fully

    Stephen Hachey

    3 W Cook, Cook Island Key, FL 33043
  • 3 W Cook, Cook Island Key, FL 33043
    3 W Cook, Cook Island Key, FL 33043
    3 W Cook, Cook Island Key, FL 33043
    /8

    $489,500

    • 2 Beds
    • 2 Baths
    • 750 Sq Ft

    3 W Cook, Cook Island Key, FL 33043

    Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfront bungalow has two bedrooms, two baths, and an additional upstairs loft with panoramic views of Cook Island, Atlantic and Coupon Bight. The house amenities include solar power, generator hookup, hot and cold water from rain collecting cistern, inverter a/c units, permitted septic system. Repairable fully

    Stephen Hachey FLAT FEE MLS REALTY

    3 W Cook, Cook Island Key, FL 33043
  • 31129 Avenue G, Big Pine Key, FL 33043
    31129 Avenue G, Big Pine Key, FL 33043
    31129 Avenue G, Big Pine Key, FL 33043
    /32

    $455,000

    • 3 Beds
    • 3 Baths
    • 844 Sq Ft

    31129 Avenue G, Big Pine Key, FL 33043

    MOTIVATED AND PRICED TO SELL. Introducing a charming and beautifully updated home in the heart of Big Pine Key. This three bedroom two and a half bathroom residence offers comfort, privacy, and modern style all within an inviting island neighborhood. Step inside to find a bright and thoughtfully renovated interior with an open living area, updated kitchen, and stylish finishes throughout. The

    Ted Stewart Truman & Co. (KW)

    31129 Avenue G, Big Pine Key, FL 33043
  • 31131 Avenue D, Big Pine Key, FL 33043
    31131 Avenue D, Big Pine Key, FL 33043
    31131 Avenue D, Big Pine Key, FL 33043
    /26

    $455,000

    • 2 Beds
    • 1 Bath
    • 754 Sq Ft

    31131 Avenue D, Big Pine Key, FL 33043

    Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Bedroom 1 bathroom with a bonus office/guest room opening to a large screened patio and spacious back yard. This Home is a true Conch home Constructed with Miami Dade Pine originally built in Key West then moved to Big Pine to join the first few homes built on. the Island. Impact doors, new shutters, new roof,

    Heather Mason Coastal Collection Real Estate Inc.

    31131 Avenue D, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    /18

    $470,000

    • Land

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

    Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    /3

    $449,000

    • Land
    • 0.34 Acre
    • $1,303,896 per Acre

    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

    Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet ready for you to enter into the ROGO system. This sale comes with a ROGO Point Letter from Monroe County for 0 Disturbed Pine worth 24 points, giving you 44 points to enter into the ROGO system to build your dream home. Seller has done the Letter of Current Site Conditions with the County as well as engineering for a house, just

    Pamela Stangler Expert Realty LLC

    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
  • 27973 Snapper Ln, Little Torch Key, FL 33042
    27973 Snapper Ln, Little Torch Key, FL 33042
    27973 Snapper Ln, Little Torch Key, FL 33042
    /25

    $474,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    27973 Snapper Ln, Little Torch Key, FL 33042

    Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy

    Bill Vaught (REO Vaught Realty LLC Vaught Realty

    27973 Snapper Ln, Little Torch Key, FL 33042
  • 701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
    /2

    $495,000

    • Land

    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042

    Rare opportunity for water front 35 ft sea wall, now vacant lot, home was removed, located in the community of Venture Out. Build your new home or install a cement slab and use the lot for your RV or rent the site to a RV user who would like to have their boats in front of their home with easy access to open water, and the marina . Beautiful views

    Debra Schoepe Berkshire Hathaway HomeServices Knight & Gardner Realty

    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    /30

    $470,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

    Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    /46

    $487,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

    Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    /52

    $425,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

    Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    /9

    $480,000

    • Land

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

    Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
  • 6 Beach Dr, Key West, FL 33040
    6 Beach Dr, Key West, FL 33040
    6 Beach Dr, Key West, FL 33040
    /9

    $472,000

    • 2 Beds
    • 1 Bath
    • 460 Sq Ft

    6 Beach Dr, Key West, FL 33040

    Rare DOUBLE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot can be cleared providing huge wide water sunset views and the ability to add dockage with shallow boating access. Located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Repair trailer that is on site under the 50% rule, or build your dream home

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 756-8747

    6 Beach Dr, Key West, FL 33040
Florida Monroe County Summerland Key

Real Estate & Homes in Summerland Key, FL under $500,000

How to Buy a Home How to Finance a Home How to Sell a Home

In Summerland Key, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 19 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Summerland Key, FL and find the perfect fit for your homeownership goals.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group